Sales Coach - Enterprise Sales at Upwork
Chicago, IL, US

Upwork ($UPWK) is the world's largest freelancing website. Each year $1.7 billion of work happens through Upwork, allowing businesses to get more done and helping professionals break free of traditional time and place boundaries and work anytime, anywhere on projects they love. At Upwork, you'll help build on this momentum. Together, we'll create economic and social value on a global scale, providing a trusted online workplace for businesses to connect with extraordinary talent and work without limits. 


As a Sales Coach, you will be responsible for the Training and Development of our Business Development Representatives. You would be responsible for ensuring our BDR New Hires successfully ramp up and are prepared to meet quota, KPI’s and Leading Metrics. The Sales Coach will also help create a dynamic learning environment and enable the BDR Team to be successful and productive on an ongoing basis. The Sales Coach will make recommendations and conduct Training based upon organizational needs within our BDR Teams. The Sales Coach will have the opportunity to contribute to building upon our Enterprise culture, Mission, Vision and Values. This is a critical role for the future success of the Upwork Sales Organization. 

Your Responsibilities:

    • Work directly with our Business Development Teams to provide Sales Coaching & Skill Building 
    • Conduct Chair-side Call Shadowing and provide timely feedback based on competencies 
    • Solicit Feedback from Sales Leadership & Managers to build specific and effective Training
    • Coach and Train regularly on Sales Methodology, Technology, Personalized Outreach 
    • Partner with Sales Leadership to craft effective materials (Scripts, Objection Handling)
    • Meet regularly with internal stakeholders to assess performance, and align on KPI’s, Leading Metrics 


What it takes to catch our eye:

    • Professional Sales Experience -  proven success in previous Sales or Sales Trainer Role
    • Desire to take Initiative, Thrive on change and comfortable with ambiguity 
    • Excellent Written, Verbal, Interpersonal Communication Skills 


How to really knock our socks off:

    • Ability to think outside the box 
    • Creative and able to brainstorm on new projects and program ideas
    • Positive, enthusiastic and seeks to make an impact within a mission driven organization



Come change how the world works.


At Upwork you’ll help shape the future of work. From our offices in San Francisco, Mountain View and Chicago, together we’re creating exciting new opportunities for a world of professionals. You’ll be part of a vibrant culture built on shared values: Inspire a boundless future of work, Put our community first, Have a bias towards action, and Build amazing teams. Along the way you’ll have fun and enjoy the perks of a people-first company: Work from Home Wednesday's, daily breakfast and lunch, regular in-office happy hours, top-notch benefits … and more. Check out Upwork’s spotlight on The Muse for a glimpse of our daily work/life balance.


Upwork is proudly committed to recruiting and retaining a diverse and inclusive workforce. As an Equal Opportunity Employer, we never discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical condition), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.